It might be a number of things. You might be letting off your edge, or flattening the board out, when you come to the wake. You might be absorbing the wake with your knees and hips. You shouldn't need to cut out too far to clear the wake. 10-15 feet max. Work on your cut in, dont hit your max speed until you reach the top of the wake and make dang sure you still have that edge cutting through it. Straighten your legs and dont let the wake make you buckle. You should feel a sudden POP! You'll get it. A trick I use with my girlfriend is to shorten the rope ten feet so the distance across the wake is not so far and she can get the feel of crossing it.

Also, if you are having the boat drive too slowly, the tabletop will get wider making it a lot harder to clear. Just make sure you're going fast enough so that the tabletop gets nice and narrow so you can clear it easily!